diff --git a/tests/debug/comms.py b/tests/debug/comms.py
index a46ad5ca..f83f90fa 100644
--- a/tests/debug/comms.py
+++ b/tests/debug/comms.py
@@ -27,6 +27,7 @@ class BackChannel(object):
         self._server_socket = sockets.create_server("127.0.0.1", 0, self.TIMEOUT)
         _, self.port = sockets.get_address(self._server_socket)
         self._server_socket.listen(0)
+        log.info("{0} created server socket on port {1}", self, self.port)
 
         def accept_worker():
             log.info(
@@ -67,8 +68,14 @@ class BackChannel(object):
         self._established.set()
 
     def receive(self):
-        self._established.wait()
-        return self._stream.read_json()
+        log.info("{0} waiting for connection to be established...", self)
+        if not self._established.wait(timeout=self.TIMEOUT):
+            log.error("{0} timed out waiting for connection after {1} seconds", self, self.TIMEOUT)
+            raise TimeoutError(f"{self} timed out waiting for debuggee to connect")
+        log.info("{0} connection established, reading JSON...", self)
+        result = self._stream.read_json()
+        log.info("{0} received: {1}", self, result)
+        return result
 
     def send(self, value):
         self.session.timeline.unfreeze()
diff --git a/tests/debugpy/test_args.py b/tests/debugpy/test_args.py
index 639615c6..b17db78f 100644
--- a/tests/debugpy/test_args.py
+++ b/tests/debugpy/test_args.py
@@ -41,6 +41,13 @@ def test_args(pyfile, target, run):
 def test_shell_expansion(pyfile, tmpdir, target, run, expansion, python_with_space):
     if expansion == "expand" and run.console == "internalConsole":
         pytest.skip('Shell expansion is not supported for "internalConsole"')
+    
+    # Skip tests with python_with_space=True and target="code" on Windows with runInTerminal
+    # because cmd.exe cannot properly handle multiline string arguments when invoking a .cmd wrapper
+    if (python_with_space and target == targets.Code and 
+        run.console in ("integratedTerminal", "externalTerminal") and 
+        sys.platform == "win32"):
+        pytest.skip('Windows cmd.exe cannot handle multiline code arguments with .cmd wrapper')
 
     @pyfile
     def code_to_debug():